UNITED STA TES ENVIRONMENT AL PROTECTION AGENCY 

WASHINGTON, D.C. 20460 

MEMORANDUM 

Date: 05-NOV-2015 

OFFICE OF 

C HEMICAL SAFETY AND 

POLLUTION PREVENTION 

ubject: Saflufenacil inion Pomegranate. Summary of Analytical Chemistry and 

Residue Da ta. 

PC Code: l 18203 DP Barcodc: D422467 

Decision No.: 493885 Registration No.: 7969-276 

Petition No.: 4F8305 Regulatory Action: Sec. 3 Registration 

Risk Assessment Type: NA Case No.: NA 

TXR No.: NA CAS No.: 372137-35-4 

MRJD No.: 49434201 40 CFR: §180.649 

From: 

H

Risk 

George 

ealth 

Assess

Effects 

F. Kramer, 

me

Di

nt 

v

Branch 

ision 

Ph.D.

(HED) 

, 

1 

Senior 

(RAB 

(7509

1

Che ) 

P

mi

) 

~~ 

Through: ldeliz Negr6n-Encamaci6n, Chemist '!1f:t "-._/,_ / 'j, /-. · , Mohsen Sahafeyan, Chemist .. 1-a· /z J- ,. . /i,., - I .c:" 

Science Advisory Council for Chemistry (ChemSAC) / /,1 

HED (7509P) 

And 

Char

RAB 

l

I

es 

, HED 

W. Smith 

(7509

Ill

P) 

, Branch Chief C ~ 

To: Kathryn Montague/Bethany Benbow, PM Team 23 

Registration Division (RD; 7505P) 

Executive Summary 

SaOufenacil (BAS 800 H) is a broad-spectrum herbicide developed by BASF. It belongs to the 

herbicide mode-of-action Group 14 (cell membrane disruptors). Saflufenacil acts through the 

inhibition of protoporphyrinogen oxidase (PPO). resulting in cell membrane damage and 

subsequent plant death. BASF bas submitted a proposal for a new use of Treev ix ~ Powered by 

Kixor1c. Herbicide (EPA Reg. No. 7969-276. a 70% ai water-dispersible granule (WG)) on 

pomegranate, directed at the base of the tree trunks while targeting emerged broad leaf weeds. 

BASF has petitioned for the establishment of permanent tolerances under 40 CFR 

§I 80.649(a)( I) for saflufenacil, including its metabolites and degradates, in or on the raw 

agricultura l commodity (RAC) listed below. Compliance with the tolerance levels specified 

Page I of9 
Satlufenacil Summary of Analytical Chemistry and Residue Data DP# 422467 

below is to be determined by measuring only the sum of saflufenacil, 2-chloro-5-[3,6-dihydro-3-

methyl-2,6-dioxo-4-(trifl uoromethyl)-1 (2H)-pyrimidiny l]-4-tluoro-N-[[ methyl( 1-

methy Jethyl)amino ]sulfonyl]benzamide, and its metabolites N-[2-chloro-5-(2,6-dioxo-4-

(trifluorometbyl)-3,6-dihydro- l (2H)-pyrimidinyl)-4-fluorobenzoyl]-N'-isopropylsulfamide and 

N-[4-chloro-2-fluoro-5-( { [(isopropylamino)sulfonyl]amino }carbonyl)phenyl]urea, calculated as 

the stoichiometric equivalent of saflufenacil in/on the following plant commodity: 

I Pomegranate 0.03 ppm 

The previously-submitted metabolism data for com, soybean, and tomato were adequate to 

elucidate the nature of the residue in plants resulting from pre-plant/pre-emergence application. 

The HED Residues of Concern Knowledgebase Subcommittee (ROCKS) determined that 

residues of concern for the tolerance expression and risk assessment consist of saflufenacil, 

M800HJ 1, and M800H35 (Memo, B. Daiss, 06-JAN-2009; 0359645). This conclusion was 

translated to perennial crops (i.e., tree fruits and tree nuts) where satlufenaci l application is 

directed to the weeds on the orchard floor (Memo, G. Kramer, 22-JUL-2009; 0349938). As the 

proposed use on pomegranate is also directed to weeds at the base of the plants, HED concludes 

that the residues of concern for the tolerance expression and risk assessment also consist of 

saflufenacil, M800H1 I, and M800H35 for this crop. 

The nature of the residue in livestock is adequately understood based on acceptable metabo.lism 

studies conducted on lactating goats and laying hens. There are no livestock feedstuffs 

associated with the proposed use; therefore. no changes in the existing tolerances for livestock 

commodities are needed. 

The petitioner previously submitted liquid chromatography/mass spectroscopy/mass 

spectroscopy (LC-MS/MS) analytical enforcement methods for the determination of residues of 

the parent and its metabolites. BASF Method 00603/02 was developed for determination of 

residues of saflufenacil and its metabolites M800Hl 1 and M800H35 in different plant matrices 

using LC-MS/MS. The limit of quantitation (LOQ) was 0.01 ppm for each analyte in food 

matrices (human consumption) and 0.025 ppm for each analyte in feed matrices (livestock 

consumption). A revised version (Method 00603/04) of the current enforcement method was 

used for the crop field trials. The method was adequate for data collection based on acceptable 

method validation and concurrent recovery data. 

The submitted magninrde of the residue data for pomegranate are adequate. There are also 

adequate storage stability data to validate the storage conditions and intervals of samples 

collected from the field trials. Quantifiable residues were not found in any RAC sample. There 

are no regulated processed commodities associated with pomegranate. 

No Codex, Canadian, or Mexican maximum residue limits (MRLs) have been established for 

saflufenacil on pomegranate. Therefore, hannonization of MRLs and U.S. tolerances is not an 

issue at this time. 

This memorandum was reviewed by two peer reviewers of the ChemSAC, per ChemSAC 

Standard Operating Procedures (SOPs). 

Regulatory Recommendations and Residue Chemistry Deficiencies 

There are no residue chemistry issues that would preclude granting the fo llowing permanent 

Page 2 of9 
Saflufenacil Summary of Analytical Chemistry and Residue Data DP# 422467 

tolerances for residues of saflufenacil and its metabolites under 40 CFR § l 80.649(a)(l ): 

I Pomegranate 0.03 ppm 

A human health risk assessment will be prepared as a separate document (DP# 426933). 

Background 

Saflufenacil is a broad-spectrum herbicide developed by BASF. It belongs to the herbicide 

mode-of-action Group 14 (cell membrane disruptors). Saflufenacil acts through the inhibition of 

PPO, resulting in cell membrane damage and subsequent plant death. Susceptible weeds develop 

symptoms within hours of application under active growing conditions. Plant death occurs 

within 3-5 days depending upon growing conditions. The chemical structure and nomenclature 

of saflufenacil and its metabolites M800Hl 1 and M800H35, and the physicochemical properties 

of the technical grade of saflufenacil are presented in Tables 1 and 2. 

Table 1. Saflufenaci l and Metabolite Nomenclature. 

Chemical Structure 

Common name 

Company experimental name 

IUPAC name 

CAS name 

CAS registry number 

End-use product (EP) 

Chemical Structure 

Common name 

Chemical name 

Chemical Structure 

Common name 

Saflufenacil 

F 

F 

F 

F Cl 

0 

BAS 800 1-J (synonyms: AC 433 379, BASF Reg. No. 4054449) 

N -[2-ch loro-4-fluoro-5-(3-methy 1-2 ,6-d ioxo-4-( tri fl uoromethy I )-3 ,6-d ihydro- I (2 H)-

pyrim id i.ny l)benzoy I ]-N-isopropy 1-N-methy lsu If amide 

2-ch loro-5-[3 ,6-d ihydro-3-methy 1-2,6-d ioxo-4-( tri fl uoromcthy I )-1 (2 /1)-pyri midi nyl)-4-

tluoro-N-[[ methyl( 1-methylethyl)amino ]sul fonyl]benzamide 

372137-35-4 

Sharpen® Powered by Kixor'° Herbicide (EPA Reg. No. 7969-278) (2.85 lb ai/gal SC 

formulation) 

M800Hl I 

F 

F 

F 

F 

0 ~ Cl 

I H 0 H 

N......._ ~/ ~ 

II 

o o err, 

N-[2-chloro-5-(2,6-dioxo-4-(trifl uoromethyl)-3,6-dihydro- I (2/-f)-pyrimidinyl)-4-

fluorobenzoyl)-N'-isopropylsulfamide 

ft F~I Cl HOH 

~ ~ N........_ ll / NYCH3 

H,N N S - H II 

0 0 CH3 

M800H35 

Page 3 of9 
Saflufenacil Summary of Analytical Chemistry and Residue Data DP# 422467 

T able l. Saflufenacil and M e tabolite Nomenclature. 

Chemical name N-r4-chloro-2-nuoro-5-( { L(isopropylamino )sulfonyl lwnino }carbonyl)phenyl)urca 

Table 2. Physicochemical Prope rties of Tech nical Grade Saflufenacil. 

Parameter Value 

Melting point Average = 189.9 °C. peak max = 193.4 °C 

pl-I 4.43 of I% solution at 25 °C 

Bulk Density (ambient 0.661 kg/L (free fall). 0.736 kg/L (packed) temp.} 

Water solubility (20 °C) in g/100 mL: 

0.0025 in water {pH = 5): 0.0014 in pH 4 buffer: 0.21 in pH 7 bufTer: not dctcnnined due 10 

degradation in pH 9 buffer 

Solvent solubility (20 °C) in g/100 mL: 

19.4 acetoni1rile: 24.4 dichloromcthane: 55.4 N,N-dimethylformamide: 27.5 acetone: 6.55 ethyl 

acetate: 36.2 tetrahydrofuran: 35.0 bu1yrolactone: 2.98 methanol: 0.25 isopropyl alcohol: 

0.23 loluene: <0.0 I 1-octanol: <0.005 n-heptane 

Vapor pressure at 20/25 °C 20 °C = 4.5 x 10·

15 Pa 

25 °C = 2.0 x 10·15 Pa 

Dissociation constant (oK.) 4.41 

Octanol/water partition Mean Log Pow = 2.6 (Pow = 368.3) coefficient 

UV/visible absorption wavelength maximum: ''''"" = 271.6 nm 

spectrum extinction coefficient: t "" 9709 L/mol-cm 

Reference: BASF Registration Document Number (DoclD) 2005/1026464. 

860.1200 Directions for Use 

BASF has submitted a draft supplemental label for ofTreevix® Powered by Kixor® Herbicide 

(EPA Reg. No. 7969-276). Information pertaining to the proposed end-use product is listed in 

Table 3. A summary of the proposed use patterns is detailed in Table 4. 

Table 3. Summa!"' of Proposed End-Use Pr od uc t. 

Reg. ai (%of Formulation Target 

Trade Name No. formulation) Type Target Crop Pests Label Date 

Treevix00 Powered 7969- 70 WG Pomegranate Broad leaf Draft label 

by Kixor® 276 weeds submitted 

Herbicide AUG-2014 

Table 4. Summary of Directions for Use of Saflufcna cil. 

App lie. 

Timing. EPA Max Single la.x Seasonal 

Type. and Reg. App. Rate (lb Max. # Apps App. Rate (lb RTI Piii Use Directions and 

Equip. No. ai/A) per year ai/A) (days) (days) Limitations 

Pomegranate 

Post, 7969- 1.0 n. oz/A 4 4.0 n. oz/A 2 1 0 The fourth application must 

Directed to 276 (0.044 lb ail A) (0. 176 lb ail A) be made during tree 

Orchard donnancy. 

Floor 

Conclusions: The submitted use directions for Treevix® Powered by Kixor® Herbicide are 

adequate to allow evaluation of the residue data relative to the proposed use. 

Page 4 of9 
Saflufenacil Summary of Analytical Chemistry and Residue Data DP# 422467 

860.1300 Nature of the Residue - Plants 

Reference List: Memo, G. Kramer, 24-JUN-2014; 0414003 

The previously submitted metabolism data for corn, soybean, and tomato were adequate to 

elucidate the nature of the residue in plants resulting from pre-plant/pre-emergence application. 

The HED Residues of Concern Knowledgebase Subcommittee (ROCKS) determined that 

residues of concern for the tolerance expression and risk assessment consist of satlufenacil, 

M800Hl 1, and M800H35 (Memo, B. Daiss, 06-JAN-2009; D359645). This conclusion was 

translated to perennial crops (i.e., tree fruits and tree nuts) where saflufenacil application is 

directed to the weeds on the orchard floor (Memo, G. Kramer, 22-JUL-2009; D349938). As the 

proposed use on pomegranate is also directed to weeds at the base of the plants, HED concludes 

that the residues of concern for the tolerance expression and risk assessment also consist of 

saflufenacil, M800Hl 1, and M800H35 for this crop. 

860.1300 Nature of the Residue - Livestock 

The nature of the residue in livestock is adequately understood based on acceptable metabolism 

studies conducted on lactating goats and laying hens. There are no livestock feedstuffs 

associated with the proposed use; therefore, no changes in the existing tolerances for livestock 

commodities are needed. 

860.1340 Residue Analytical Methods 

Reference List: Memo, G. Kramer, 24-JUN-2014; 0414003 

BASF Method D0603/02 is the current enforcement method for determination of residues of 

satlufenacil and its metabolites M800Hl 1 and M800H35 in different plant matrices. Residues of 

saflufenacil and its metabolites M800Hl 1 and M800H35 were extracted with methanol:water 

(70:30; v:v). The methanol extract was evaporated and reconstituted in methanol:water (50:50; 

v:v) for LC-MS/MS analysis. Two transitions per analyte were monitored for the quantitation 

and confirmation of saflufenacil, M800H 11 and M800H35. The residues of each analyte were 

expressed as parent equivalents using a molecular weight conversion factor (1.0 for saflufenacil, 

1.06 for M800Hl 1, and 1.42 for M800H35). The LOQ was 0.01 ppm for each analyte. The 

limit of detection (LOD) was reported to be 3X the standard deviation (SD) at the LOQ for each 

analyte (0.002-0.003 ppm). 

A revised version (Method D0603/04) of the current enforcement method was used for the crop 

field trials. Method D0603/04 has been revised from the established enforcement method, 

Method 00603/02, to add instructions for determination of metabolite M800H02 (N-[2-chloro5-(2, 6-di oxo-4-( trifl uoromethy l )-3 ,6-dihydro-l (2H)-pyrimidiny 1)-4-fl uorobenzoyl ]-N-isopropy 1-

N-meth y lsul famide). A complete method description and method validation data for Method 

D0603/04 were included in MRJD# 49312401. In support of the revised method, BASF has also 

submitted the results of an IL V of the method (MRJD# 49118203). Method D0603/04 is 

adequate for data collection in the submitted field trials based on acceptable concurrent recovery 

data. Recoveries were generally within the acceptable range of 70-120%. As the dataacquisition method is essentially identical to the enforcement method with regards to the residues 

of concern and it was successfully validated, HED concludes that an adequate enforcement 

Page 5 of9 
Saflufenacil Summary of Analytical Chemistry and Residue Dara DP# 422467 

method is available to enforce a tolerance for residues of saflufenacil in pomegranate. 

860.1360 Multiresidue Methods (MRM) 

Saflufenacil and its metabolites M800Hl I and M800H35 were screened through the MRM 

described in the United States Food and Drug Admjnistration (FDA) Pesticide Analytical 

Manual, Vol. I (PAM I). Saflufenacil and the metabolites were tested using procedures outlined 

in Protocols B, C, D, E, and F of the MRM. All Protocols B, C, D, E, and F were found to be 

unsuitable for determination of residues of saflufenacil and its metabolites M800Hl 1 and 

M800H35. Since the analytes are not N-methyl-carbarnates, naturally fluorescent or substituted 

urea derivatives, the tests using Protocol A and G were not performed. 

860.1380 Storage Stability 

The field residue samples were stored frozen a maximum of33 days (1. l months) from harvest 

to extraction. All samples were analyzed within 1 day of ex'traction. Adequate storage stability 

data are available in/on various crop commodities (com (grain, forage, stover); soybean (seed, 

forage, hay); orange (fruit, pulp, juice, oil); radish (root); grape (raisin); and garbanzo bean 

(seed)] indicating that residues of saflufenacil, M800Hl 1, and M800H35 are stable in/on alJ 

tested commodities during frozen storage for up to 548 days (MRID No. 47523801). These data 

are acceptable to support the storage conditions and durations of samples from the submitted 

field trials for residues of saflufenacil, M800H 11 , and M800H35. 

860.1480 Meat, Milk, Poultry, and Eggs 

There are no livestock feedstuffs associated with lhe proposed use; therefore, no changes in the 

existing tolerances for livestock commodities are needed. 

860.1500 Crop Field Trials 

DER Reference List 4943420 I .der.docx 

Four field trials were conducted in the United States during the 2013 growing season in the 

North American Free Trade Agreement (NAFT A) Growing Zone I 0 (CA). Each trial consisted 

of one untreated plot and one treated plot. At each trial location, the treated plot received four 

banded ground applications of a 70% WG formu lation of saflufenaciJ (BAS 800 OlH). The 

applications were made to the ground of the pomegranate orchard (beneath the trees and/or i.n 

areas between rows) at 0.0433-0.0466 lb ai/A/application, for a total seasonal rate of 0.177-0. I 82 

lb ai/A (lX). The first application was made in February during wi.nter dormancy (prior to 

spring bud break or onset of flowering) fol lowed by three applications made at fruiting. 

Retreatrnent intervals (RTis) were 189-201 days between the first and second applications and 

20-21 days between the second, trurd, and fourth applications. Applications were made using 

ground equipment in spray volumes of- 15-37 gal/A. A methylated seed oil (MSO) was added 

to the spray mixture for each of the applications. Samples of pomegranate were harvested at a Oday PHI. 

Page 6 of9 
Sanufenacil Summary of Analytical Chemistry and Residue Data DP# 422467 

Following four banded ground applications of the 70% WO fom1ulation of saflufenacil at a total 

seasonal rate of0.177-0.182 lb ai/A, combined residues (and per-trial averages) ofsaflufenacil, 

M800H l l, and M800H35 were below the LOQ (<0.03 ppm) in/on all san1ples of pomegranate 

harvested at a 0-day PHI (Table 5). Residue decline was not investigated. Residues of 

M800H 11 and M800H35 were not converted to parent equivalents because they were <LOQ. 

Table S. S umma r y of Residues from Pomegranate Field Trials with Sanufeoacil. 

Total Residues (ppm) 

Application 

Rate Pl-11 

Crop Matrix Analytt: (lb ai/A) (days) nl Min. 2 Max .~ Ll\FT3 l-LAFT3 Median3 Mean3 SD' 

Pomegranate Sanufenacil 0. 177-0.182 0 4 <0.0 1 <0.0 1 <0.01 <0.01 0.01 0.01 NIA 

M800111 l 4 <0.0 1 <0.0 1 <0.01 <0.01 0.01 0.01 NIA 

M800H35 4 <0.0 1 <0.01 <0.01 <0.01 0.01 0.0 1 NIA 

Combined Residues4 4 <0.03 <0.03 <0.03 <0.03 0.03 O.Q3 NIA 1 n = number of fi eld trials. 

~ Values based on total number of samples. 3 Values based on per-trial averages. LAFT =lowest average lield trial, l IAFT = highcs1 average field trial. SD = standard 

deviation. For computation of the LAFT. HAFT. median, mean, and standard deviation. values <LOQ are assumed to be at the 

LOQ (0.0 I ppm). N/ A = not applicable. 4 Combined residues of sallufenacil. M800H 11 , and M8001-135. 

Conclusions: The submitted residue data are adequate to fulfill data requirements for 

pomegranate. The number and locations of the crop field trials are in general accordance with 

OCSPP Guideline 860.1500 (Table 6). The available data will support the proposed use pattern. 

Table 6. Trial N umbe rs and Geograph ical Locations. 

o. NAFT A Growing Zone 

Crop Trials I 2 3 4 5 6 7 8 9 10 11 12 Total 

Pomegranate Sub. 4 4 

Rcq. 1 3 or2 

1 As per Table I of 860.1500 for pomegranate, 1hree trials with a minimum of 6 srunplcs or 1wo trials with a minimum of 8 

samples arc required. Geographic distribution is not specified for crops requiring $3 !rials: however. per Table 6 of 860.1500. 

Zone I 0 accounis for 99% of U.S. pomegranate production. 

The residue data for pomegranates were not entered into the Organization for Economic Cooperation and Development (OECD) MRL (maximw11 residue limit) Calculator as all of the 

residues were <LOQ. The recommended tolerance for the combined residues of satlufenacil and 

its metabolites M800Hl 1 and M800H35, expressed as parent equi valents, is 0.03 ppm for 

pomegranate. 

860.1520 Processed Food and Feed 

There are no regulated processed commodities associated with pomegranate. 

Page7of9 
Satlufenacil Summary of Analytical Chemistry and Residue Data DP# 422467 

860.1650 Submittal of Analytical Reference Standards 

Analytical standards of saflufenacil (expiration date: 511114), M800Hl l (metabolite 5303307; 

expiration date: 7/ 1/14), and M800H35 (metabolite 5303308; expiration date: 7/1/ 14) are 

currently available in the National Pesticide Standards Repository [source: personal 

communication with T. Cole of ACL/BEAD, 3/6/14]. The registrant subsequently recertified the 

lots in the repository and submitted updated Certificates of Analysis for saflufenacil (expiration 

date: 2/1/18). 

860.1850/860.1900 Confined/Field Accumulation in Rotational Crops 

Rotational crop studies are not germane to this petition as pomegranates are not rotated with 

other crops. 

860.1550 Proposed Tolerances 

BASF has petitioned for the establishment of permanent tolerances 40 CFR §I 80.649(a)( 1) for 

saflufenacil, including its metabolites and degradates, in or on the agricultural commodity listed 

below. Compliance with the tolerance levels specified below is to be determined by measuring 

only the sum of saflufenacil, 2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-

1 (2ff)-pyrimidinyl]-4-fluoro-N-[[ methyl(l-methylethyl)amino ]sulfonyl]benzamide, and its 

metabolites N-[2-chloro-5-(2, 6-dioxo-4-( trifluoromethyl )-3 ,6-dihydro-1 (2ff)-pyrirnidinyl)-4-

fl uoro benzo yl ]-N -isopropy lsulfamide and N-[4-chloro-2-fluoro-5-

( { [ (isopropylarnino )sulfonyl]amino} car bony l)pheny l]urea, calculated as the stoichiometric 

equivalent of saflufenacil inion the following plant commodity: 

Table 7. Tolerance umm ~ for Saflufenacil. 

Proposed HED-Recommended Correct Commodity 

Conunodity Tolerance (nnm) Tolerance (ppm) Definition/Comments 

Pome!rranate 0.03 0.03 

HED is not recommending for any revision to the petitioned-for tolerance (see Table 7): 

No Codex, Canadian, or Mexican MRLs have been established for saflufenacil on pomegranate. 

Therefore~ harmonization of MRLs and U.S. tolerances is not an issue at this time. 

List of Attachments 

Attachment I. International Residue Limit Status (IRLS) sheet. 

cc: G. Kramer (RAB I) 

ROI: RABI Chemists (5/6/ 15) 

G.F. Kramer: SI 0957:PY-S:(703)305-5079:7509P:RAB I 

Page 8 of9 
Saflufenacil Summary of Analytical Chemistry and Residue Data DP# 422467 

Attachment 1. IRLS Sheet. 

International Residue Limits Status 

s a fl u u enac il (I 1820" J; D ate o f R equest: 4/24/2015) 

Summary of U.S. and lntemationaJ Tolerances and Maximum Residue Limits 

Residue Definilion: 

U.S. Canada Mexico2 Codex 

40 CFR 180.649: 2-chloro-5-[3,6-dihydro-3-methyl- Saflufenacil 

Plant: saflufenacil, including its 2,6-dioxo-4-(tri fluoromethyl)- The residue 

metabolites and degradates, sum of I (2H)-pyrimidinyl)-4-fluoro-N- is not fat 

saflufenacil, 2-chloro-5-(3,6- [[ methyl{I - soluble 

d ihydro-3-methyl-2,6-d ioxo-4- methy lethyl)arn ino ]su I fonyl)benzam 

(rri fluoromethyl)-1 (2H)- ide, including the metabolites N'-{2-

pyrim id inyl]-4-fluoro-N- chloro-4-fluoro-5-[ 1,2,3,6-

[[methyl( I- tetrahydro-2,6-dioxo-4-

met hy lethyl)am ino Jsu I fonyl)benza (trifluoromethyl)pyrimidin- 1-

mide, and its metabolites N-[2- yl]benzoyl}-N-isopropyl sulfamide 

chloro-5-(2,6-dioxo-4- and N-[4-chloro-2-fluoro-5-

(trifluoromethyl)-3,6-dihydro- ( {[(isopropylamino )sulfonyl] 

I (2H)-pyrimidinyl)-4- amino} carbony l)phenyl]urea 

fluorobenzoyl]-Nisopropylsulfamide and N-[4- Livestock: 2-chloro-5-[3,6-dihydrochloro-2-fluoro-5- 3-methyl-2,6-dioxo-4-

( { [(isopropylamino )sulfonyl]amino (trifluoromethyl)-1 (2H)-

}carbonyl)phenyl]urea, calculated pyrimidinyl)-4-tluoro-N-[[methyl( Ias the stoichiometric equivalent of methylethyl)amino ]sulfonyl]benzam 

saflufenacil ide 

Comnwdity1 Tolerance (ppm)/Maximum Residue Limit (mg/ kg) 

U.S. Canada Mexico2 Codex 

Pomegranate 0.03 

Completed: M. Negussie; 04/24/15 

1 Includes only commodities of interest for this action. Tolerance values should be the HED recommendations and 

not those proposed by the applicant. 

2 Mexico adopts U.S. tolerances and/or Codex MRLs for its expon purposes. 

Page 9 of9 
Satlufenacil/ PC Code 118203/Jnterregional Research Project No. 4 

B.7.6 Residues Resulting from Supervised Trials 

(Annex HA 6.3; Annex IITA 8.3) 

B. 7.6.1 Residues in Target Crops 

B.7.6.l.J Pomegranate 

Report: 

Guidelines: 

GLP Compliance: 

Acceptability: 

Evaluator: 

otc: This DER was originally prepared under contract by Versar. Inc. (6850 Versar Center. Springfield, VA 22 151; submitted 

3/6/ 15). The DER has been reviewed by HED and revised to reflect current Office of Pesticide Programs (OPP) policies. 

EXECUTIVE SUMMARY 

The Interregional Research Project Number 4 (IR-4) has submitted field trial data for satlufenacil 

on pomegranate. Four field trials were conducted in the United States during the 2013 growing 

season in the North American Free Trade Agreement (NA.FT A) Growing Zone 10 (CA). 

Each trial consisted of one untreated plot and one treated plot. At each trial location, the treated 

plot received four banded ground applications of a 70% water-dispersible granule (WO) 

formu lation of satlufenacil (BAS 800 OIH). The applications were made to the ground of the 

pomegranate orchard (beneath the trees and/or in areas between rows) al 0.0433-0.0466 lb 

ai/Napplication, for a total seasonal rate of 0.177-0.182 lb ai/A. The first application was made 

in February during winter dormancy (prior to spring bud break or onset of flowering) followed 

by three applications made at fruiting. Retreatment intervals (RTis) were 189-201 days between 

the first and second applications and 20-2 l days between the second, third, and fourth 

applications. Applications were made using ground equipment in spray volumes of- 15-37 

gal/A. A methylated seed oil (MSO) was added to the spray mixture for each of the applications. 

Samples of pomegranate were harvested at a 0-day preharvest interval (PHI). 

Pa e I of7 

MRID# 4943420 I 
Satlufenacil/PC Code 118203/Interregional Research Project No. 4 

All samples were maintained frozen at the testing facilities, during shipping to the laboratory, 

and were stored frozen until analysis. The field residue samples were stored frozen for a 

maximum of 33 days (1.1 months) from harvest to extraction. All samples were analyzed within 

l day of extraction. Adequate storage stability data are available (DP#349938, 7/22/09, G. 

Kramer) indicating that residues of saflufenacil and its metabolites M800Hl 1 and M800H35 are 

stable during frozen storage for up to 548 days in/on various crop commodities including: com 

(grain, forage, stover); soybean (seed, forage, hay); orange (fruit, pulp, juice, oil); radish (root); 

grape (raisin); and garbanzo bean (seed). These data are acceptable to support the storage 

conditions and durations of samples from the submitted field trials. 

Samples were analyzed for residues of saflufenacil and metabolites M800H 11 and M800H35 

using a high-performance liquid chromatography method with tandem mass-spectrometry 

detection (LC/MS/MS), Method 00603/04, which is essentially identical to the enforcement 

analytical method for saflufenacil in plants. Acceptable concurrent recoveries were reported for 

samples of pomegranate fortified with each analyte at 0.01-1.0 ppm, thus validating the method. 

The limit of quantitation (LOQ; determined as the lowest level of method validation, LLMV) 

was 0.01 ppm for each analyte, for a combined LOQ of 0.03 ppm (metabolite residues not 

expressed in parent equivalents). The fortification levels used in concurrent method recovery 

were adequate to bracket expected residue levels. Recoveries and residues in treated samples 

were not corrected for residues in controls. 

Following four banded ground appli cations of the 70% WG formulation of saflufenacil at a total 

seasonal rate of 0.177-0.182 lb ai/A, combined residues (and per-trial averages) of saflufenacil, 

M800Hl 1, and M800H35 were below the LOQ ( <0.03 ppm) inion all samples of pomegranate 

harvested at a 0-day PHI. Residue decline was not investigated. Residues of M800H 11 and 

M800H35 were not converted to parent equivalents because they were <LOQ. 

I. MATERIALS AND METHODS 

A. MATERIALS 

Table B.7.6.1.1-1. Nomenclature for Saflufenacil and Metabolites oflnterest. 

Chemical Structure F Cl 

0 ~ CH, I H 0 I :::::-..... N'-..~/NYCH, 

I 

N 

N~O II 

f 0 0 CH, 

F I 

F CH, 

Common name Saflufenacil 

Company experimental name BAS 800 H (synonyms: AC 433 379. BASF Reg. No. 4054449) 

lUPAC name N'-[2-ch loro-4-lluoro-5-(3-methyl-2, 6-dioxo-4-( trifl uoromethy I )-3 ,6-d ihydro-1 (2/-/)-

pyrimidinyl)benzoyl]-N-isopropyl-N-methylsulfamide 

CAS name 2-ch Joro-5-(3 ,6-dihydro-3-methyl-2,6-d i oxo-4-( tri fl uoromethy 1)- 1 (211)-pyrim id i ny I ]-4-

fl uoro-N-[[ me thy I( 1-methy lethy I )amino ]su lfonyl] benzam ide 

CAS registry number 372137-35-4 

End-use product (EP) Sharpen® Powered by Kixor® Herbicide (EPA Reg. No. 7969-278) {2.85 lb ai/gal SC 

formulation) 

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MRJD# 4943420 I 
Saflufenacil/ PC Code 118203/lnterregional Research Project No. 4 

Table B.7.6. 1.1 - 1. Nomenclature for Saflufenacil and Metabolites oflnterest. 

Chemical Structure 

Common name M800Hl I 

F 

F 

F 

0 

F 

H 0 H 

,~_......Nye~ 

II 

o o c~ 

Chemical name N-[2-ch loro-5-(2.6-d ioxo-4-( tri n uoromcth y 1)-3 .6-d ihydro-I (2 H)-pyri midi ny I )-4-

tl uorobcnzoy l]-N'-isopropyl su I famide 

Chemical Structur..: F 

Common name M800H35 

Chemical name N-f 4-ch loro-2-n uoro-5-( { f ( isopropy lam i no )su I fony !lam ino} carbony l)pheny I] urea 

B. Study Design 

1. Test Procedure 

Four residue trials in/on pomegranate were conducted with a 70% WG formulation of 

saflufenacil (BAS 800 OIH) during the 2013 growing season. Field trial locations by NAFTA 

growing zone are summarized in Table B.7.6.J. l-2. 

The trials separated by <20 miles have been assessed for independence as detailed in the table 

below. Because the geographic area suitable for pomegranate cultivation in the U.S. is limited, 

HED has concluded that these trials may be considered separate trials for purposes of 860.1500 

data requirements. 

Independent Trial Determination' 

Crop Trial Nos. fferences~ Decision 

Pomegranate 13-CA02 & 13-CA03 Sarne location and varietv Separate 

Timing: 7- to 8-day olT-sct in application and harvest 

Sprav volume: - 15 GPA vs. - 33 GPA 

*No other dilTercnces in criteria 1 All assessments are based on the replicate trial guidance presented in draft memo 568_Criteria for Independence of Trials 

04/2312013 (EPA and PMRA). 

? The petitioner indicated that the CA02 & CA03 trials were differentiated by separate spray solutions prepared, >25% dilTerence 

between spray rates, different fcnilizers within spray mix (an1monium sulfate vs. urea ammonium nitrate). and backpack sprayer 

vs. tractor-mounted spray equipment being used at the same location. 

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Sanufenacil/PC Code 118203/lnterregional Research Project No. 4 

Table B.7.6.1.1-2. Trial Numbers and Geographical Locations. 

No. NAFTA Growing Zone 

Crop Trials I 2 3 4 5 6 7 8 9 10 II 12 Total 

Pomegranate Sub. 4 4 

Rcq.

1 3 or2 

1 As per Table I of 860.1500 for pomegranate. three trials with a minimum of 6 samples or two trials with a minimum of 8 

samples are required. Geographic distribution is not specified for crops requiring 9 trials: howc\'er. per Table 6 of 860.1500. 

Zone I 0 accounts for 99% of U.S. pomegranate production. 

Locations and detailed use patterns for the trials are provided in Table B.7.6.1.1-3. 

Table B.7.6. 1.1-3. Study Use Pattern. 

Location: City. Rate per Reirealment 

Staie; Year End-use Method of Application: Timing Volume /\pplication 

(Trial ID) Product1 of /\pplicalion (gal/A) (lb ai/A) 

Parlier. CA: 70%WG I. Banded to the ground: 15.2 0.0439 

2013 dormant 

(13-CA02) 2. Banded to the ground: fruiting 14 .9 0.044 1 

3. Banded lo the ground: fruiting 15.0 0.0446 

4. Banded to the ground: fruiting 15.0 0.0446 

Parlier. CA: 70% WG I. Banded to the ground: 30.5 0.0446 

201 3 dormant 

( 13-C/\03) 2. Banded to the ground: fruiting 32.6 0.0-1 53 

3. Banded to the ground: fruiting 31.8 0.0444 

4. Banded to the ground: fruiting 33.0 0.0465 

Davis. CA: 70%WG I. Banded 10 the ground: 32.0 0.0-138 

2013 dormant 

( 13-CA04) 2. Banded to the ground: fruiting 35.8 0.0449 

3. Banded to the ground: fmiting 37.I 0.0465 

4. Banded to the ground: fmiting 37.2 0.0466 

Yuba City. CA: 70%\VG I. Banded 10 ll1e ground; 16.8 0.0433 

2013 dormant 

( 13-C/\05) 2. Banded to the ground: fruiting 17.6 0.0453 

3. Banded to the ground; fruiting 17.6 0.0453 

4. Banded to the ground: fruiting 17.2 0.0443 

1 70% WG formulation ofsaflufcnacil (BAS 800 01 H: Trcevix Powered by Kixor Herbicide). 2 MSO = methylated seed oil. 

Interval 

(days) 

--

201 

2 1 

20 

--

201 

21 

21 

--

197 

2 1 

20 

--

189 

21 

20 

Total Rate 

(lb ai/A) 

0. 177 

0.181 

0.182 

0.178 

Surfactant/ 

Adjuvant2 

MSO 

MSO 

MSO 

MSO 

Pomegranates were grown and maintained according to typical agricultural practices. Irrigation 

was used to supplement rainfall as needed at all trial sites. No w1Usual weather conditions were 

reported during the study. 

Sample Handling and Preparation 

Duplicate control and treated samples of pomegranates were harvested on the day of the final 

application after the spray had dried (0-day PHI). The pomegranates were quartered and either 

one quarter or opposite quarters were retained as samples. Samples were placed in frozen 

storage at the field sites within - 2.75 hours of collection and were shipped frozen within 5-1 6 

days of coll ection by overnight carrier on dry ice to the analytical laboratory, BASF Crop 

Protection (Research Triangle Park, NC) for residue analysis. Samples were maintained frozen 

(- -8 °C) at the analytical laboratory prior to homogenization and analysis. In preparation for 

analysis, samples were ground in the presence of dry ice. 

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MRID# 49434201 
Saflufenacil/PC Code 118203/lnterregional Research Project No. 4 

2. Description of Analytical Procedures 

Samples were analyzed for residues of saflufenacil and its metabolites M800H 11 and M800H35 

using LC/MS/MS, Method D0603/04, which is essentially identical to the enforcement analytical 

method for saOufenacil in plants, Method D0603/02, that was previously reviewed by the 

Agency (DP# 349938, 7/22/09, G. Kramer). A complete description of the method was included 

in the submission. 

Briefly, residues of saflufenacil, M800Hl 1, and M800H35 were extracted with methanol:water 

(70:30; v:v). An aliquot of the extract was concentrated, and residues in the aqueous remainder 

were acidified with 0.1 M trifluoroacetic acid (TFA) and then partitioned with ethyl 

acetate:cyclohexane (70:30; v:v). An aliquot of the organic phase was evaporated and 

reconstituted in methanol:water (50:50; v:v) for LC/MS/MS ana lysis. 

The LOQ, detenn ined as the LLMV, was 0.01 ppm for each analyte in pomegranates, for a 

combined LOQ of 0.03 ppm (metabolite residues not expressed in parent equivalents). The 

petitioner stated that the limit of detection (LOD) was 20% of the LOQ (0.002 ppm) per analyte. 

II. RESULTS AND DISCUSSION 

Method performance was evaluated by use of concurrent recovery samples. Samples of 

untreated pomegTanates were fortified with satlufenacil, M800Hl I, and M800H35 at 0.01 and 

1.0 ppm each. Recoveries were generally within the acceptable range of 70-120%; therefore, the 

method was considered valid for the analysis of saflufenacil, M800H 11 , and M800H35 residues 

in pomegranates (Table B.7.6.1.1-4). The fortification levels bracketed the measured residues. 

Concurrent recoveries were not corrected for apparent residues in controls. 

The detector response was linear (coefficient of determination, r2 2:0.9813) within the range of 

0.025-0.50 ng/mL. Representative chromatograms of control samples, fortified samples, and 

treated samples were provided. The control chromatograms generall y had no peaks of interest 

above the chromatographic background. The fortified sample chromatograms contained only the 

analyte of interest, and peaks were symmetrical and well defined. Apparent residues in controls 

were below the LOQ in/on all samples. The reported residue values were not corrected for 

apparent residues in controls. Residues ofM800Hl 1 and M800H35 were not converted to 

parent equivalents because all residues were nonquantifiable. 

Table B. 7.6. 1.1-4. Summary of Procedural/Concurrent Recoveries of Saflufe nacil a nd its Metabolites 

M800H 11 and M800H35 from Pomegranate. 

Fortification Sample 

Matrix Analyte Level (ppm) Size (n) Rccovc:ries1 (% ) 

Pomegr-.matc Saflufcnacil 0.01-1.0 2 

M800Hl I 0.01-1.0 2 

M800H35 0.01 -1.0 2 1 Concurrent rccovt:ries wt:re not corrected for apparent residues in controls. 2 Standard deviation is not calculated for sample sizes <3. 

90. 90 

92.93 

68: 100 

Mean ± Std. Dev.2 

(%) 

90 

93 

84 

The field residue samples were stored frozen a maximum of 33 days ( 1.1 months) from harvest 

to extraction (Table B.7.6.1.1 -5). All samples were analyzed within I day of extraction. 

Adequate storage stability data are available (DP#349938, 7/22/09, G. Kramer) indicating that 

residues of saflufenacil and its metabolites M800Hl l and M800H35 are stable during frozen 

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MRID# 49434201 
Saflufenacil/PC Code 118203/lnterregional Research Project No. 4 

storage for up to 548 days in/on various crop commodities including: corn (grain, forage, 

stover); soybean (seed, forage, hay); orange (fruit, pulp, juice, oil); radish (root); grape (raisin); 

and garbanzo bean (seed). These data are acceptable to support the storage conditions and 

durations of samples from the submitted field trials. 

Table B.7.6.1.1-5. Summa r y of Stor age Conditions. 

Storage Actual Storage 

Matrix Temperature (°C) Duration1 Interval of Demonstrated Storage Stability 

Pomegranate fruit -8 20-33 days Residues of saflufenacil and its metabolites M800H I I and 

(0.9-1.1 months) M800H35 are stable during frozen storage for up to 548 days in/on 

various crop commodities including: corn (grain, forage, stover); 

soybean (seed, forage, hay); orange (fruit, pulp, juice. oil); radish 

(root); grape (raisin); and garbanzo bean (seed).2 

1 Interval from harvest to extraction. Samples were analyzed w1thm I day of extraction. 2 OP#349938, 7122109, G. Kramer. 

The results from the submitted field trials are presented in Tables B.7.6. 1.1-6 and B.7.6.1.1-7. 

Following four banded ground applications of the 70% WG formulation of satlufenacil at a total 

seasonal rate of 0.177-0.182 lb ai/A, combined residues (and per-trial averages) of satlufenacil, 

M800Hl 1, and M800H35 were below the LOQ (<0.03 ppm) in/on all samples of pomegranate 

harvested at a 0-day PHI. Residue decline was not investigated. Residues of M800Hl 1 and 

M800H35 were not converted to parent equivalents because they were <LOQ. 

Table B. 7.6.1.1 -6. R esidue Data from Pomegrana te Field Trials w ith Saflufenacil.1 

Location: City. Residues2 (ppm) [Average] 

State; Year (Trial Crop Rate PHI Combined 

ID) Zone Variety Matrix (lb ai/A) (days) Saflufenacil M800H I 13 M800H353 Residues4 

Parlier, CA; 2013 10 Wonderful Fruit 0.177 0 ND,ND ND,ND ND,ND <0.03, <0.03 

(13-CA02) [<0.01] [<0.0 1] [<0.01] [<0.031 

Parlier, CA: 2013 10 Wonderful Fruit 0. 181 0 ND, ND ND,ND ND, ND <0.03. <0.03 

( 13-CA03) [<0.01] [<0.0 1] [<0.01] [<0.03] 

Davis, CA: 2013 10 Wonderful Fruit 0. 182 0 ND.ND ND. ND ND.ND <0.03. <0.03 

( 13-CA04) [<0.0 I] [<0.01] [<0.01] [<0.03] 

Yuba City. CA; 10 Wonderful Fruit 0.178 0 ND.ND ND.ND ND.ND <0.03. <0.03 

2013 ( 13-CAOS) [<0.01] [<0.01] [<0.01] [<0.03] 

1 A 70% WG formulation of saflufenacil (BAS 800 01 H) was used. 2 ND = not detected (<LOO). The LOO was 0.002 ppm. and the LOQ was 0.0 I ppm for each analyte. Per-trial averages were 

calculated by the petitioner and assumed LOQ residues for samples <LOQ. 3 Residues of M800H 11 and M800H35 were not converted to parent equivalents because they were <LOQ. 

J Combined residues of saflufenacil, M800H I I, and M800H35 (metabolites are not expressed in parent equivalents). 

T able B.7.6.1.1-7. Summary of Residues from P omeg ra na te F ield T ria ls with Saflufenacil. 

Total Residues (ppm) 

Application 

Rate PH L 

Crop Matrix Analyte (lb ai/A) (days) n' Min.2 Max.2 LAFT3 HAFT3 Median3 Mean3 SD3 

Pomegranate Safl u fenaci I 0.177-0.182 0 4 <0.01 <0.01 <0.01 <0.01 0.01 0.01 NIA 

M800H I I 4 <0.01 <0.01 <0.01 <0.01 0.01 0.01 NIA 

M800H35 4 <0.01 <0.0 1 <0.01 <0.01 0.01 0.01 NIA 

Combined Residues4 4 <0.03 <0.03 <0.03 <0.03 0.03 0.03 NIA 

1 n = number of field trials. 2 Values based on total number of samples. 3 Values based on per-trial averages. LAFT = lowest average field trial. HAFT = highest average fie ld trial. SD = standard 

deviation. For computation of the LAFT, HAFT, median, mean, and standard deviation, values <LOQ arc assumed to be at the 

LOQ (0.0 I ppm). NIA = not applicable. 4 Combined residues of satlufenaeil, MSOOH 11 , and M800H35. 

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MRlD# 4943420 I 
SaOufenacil/PC Code I 18203/lnterregional Research Project No. 4 

Ill. CONCLUSIONS 

The submitted pomegranate field trial data are adequate. Following four banded ground 

applications of the 70% WG formulation of saflufenacil at a total seasonal rate of 0.177-0.1 82 lb 

ai/ A, combined residues (and per-trial averages) of saflufenacil, M800H 11, and M800H35 were 

below the LOQ ( <0.03 ppm) inion all samples of pomegranate harvested at a 0-day PHI. 

Residue decline was not investigated. Residues of M800Hl 1 and M800H35 were not converted 

to parent equivalents because they were <LOQ. 

An acceptable method was used for residue quantitation, and adequate storage stability data are 

available to support sample storage durations and conditions for all analytes. 

REFERENCES 

DP# 349938, 7/22/09, G. Kramer. 

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M RJ D# 4943420 I